• Leeward Islands baech chairs
  • Leeward Islands tropical fish
  • Leeward Islands coastline
  • Leeward Islands cottages

Leeward Islands Sample Itinerary

Day 1: St. Maarten

Begin your yacht charter vacation by boarding on the Dutch side of St. Maarten at the beautiful Simpson Bay Marina, located just minutes from the international airport and within walking distance to duty-free shopping and several restaurants. Relax onboard in the Caribbean sunshine, or venture along the waterfront enjoying the sights and sounds of the turquoise lagoon with its spectacular array of super yachts in various shapes and sizes.

Day 2: St. Barth's

After breakfast, depart St. Maarten for a two-hour cruise south to the Caribbean's most luxurious island, St Barth's. Drop anchor in beautiful Anse de Colombier and take a refreshing dip in the ocean, marveling at the captivating resident sea turtles. In the afternoon head to the gorgeous sand dunes and crystal clear waters of Saline Beach.

Day 3: St. Barth's

After breakfast, head to the main port and capital town of Gustavia for a day of shopping in its chic boutiques, duty-free shops and art galleries. Enjoy world famous restaurants offering everything from the best in French cuisine to open-air bars housed in buildings that date back to the early French settlers. Situated along the waterfront, make sure to stop by Le Select, the inspiration behind Jimmy Buffet's "Cheeseburger In Paradise." If you're lucky, he may even stop in for an impromptu jam session.

Day 4: Saba

A short hop from St. Barth's is the picturesque Dutch island of Saba. Enjoy an afternoon hike to the top of Mount Scenery, a potentially active volcano reaching almost 3,000 feet. The beautiful flora and fauna of the island will take your breath away. For lunch, stop in at one of the neighboring eateries offering the best in local seafood.

Day 5: Anguilla

Head to the beautiful low-lying island of Anguilla, known for its white sand beaches and beautiful palm trees. Curl up in a hammock and enjoy the balmy Caribbean breeze, or take a stroll along the sugar sand beaches and watch in awe as local fishermen bring in their daily catch.

Day 6: Anguilla

Head out for an afternoon trip to the beautiful Prickly Pear cays for a private lunch of grilled lobster and local caught fish. Swim in the turquoise water and snorkel with sea turtles, rays and tropical fish. These cays capture the true essence of the Caribbean.

Day 7: Grande Case, St. Maarten

On your final day of charter, spend the day at anchor in Grande Case, St. Maarten. Have the crew take you wakeboarding, or go paddleboard over the clear turquoise water. For dinner, head into town and enjoy the sights and sounds of this beautiful French-Caribbean city. With open-air restaurants, live music and beautiful art crafted by the locals, this gem of St. Maarten should not be missed.